# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_iran-a51
_database_code_depnum_ccdc_archive 'CCDC 1878041'
loop_
_audit_author_name
_audit_author_address
'Alireza Salimi'
;Ferdowsi University of Mashhad
Iran
;
_audit_update_record             
;
2018-11-09 deposited with the CCDC.	2019-09-23 downloaded from the CCDC.
;
_audit_creation_date             2015-04-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H10 N2 O2'
_chemical_formula_sum            'C15 H10 N2 O2'
_chemical_formula_weight         250.25
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   7.73077(13)
_cell_length_b                   25.6327(4)
_cell_length_c                   5.93311(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1175.71(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9501
_cell_measurement_temperature    100
_cell_measurement_theta_max      76.0730
_cell_measurement_theta_min      3.3770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.786
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72021
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            17169
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.058
_diffrn_reflns_theta_min         3.448
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2603
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
?
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1577664000
_diffrn_orient_matrix_UB_12      -0.0315494000
_diffrn_orient_matrix_UB_13      0.0814237000
_diffrn_orient_matrix_UB_21      0.0136420000
_diffrn_orient_matrix_UB_22      0.0352225000
_diffrn_orient_matrix_UB_23      0.2095104000
_diffrn_orient_matrix_UB_31      -0.1209518000
_diffrn_orient_matrix_UB_32      -0.0371261000
_diffrn_orient_matrix_UB_33      0.1298656000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.800
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                2337
_reflns_number_total             2437
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 1017 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.01(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2437
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0297
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0465P)²+0.2111P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0797
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.6094(2) -0.75207(5) 0.0771(3) 0.0301(3) Uani 1 1 d . . . . .
O2 O -0.45214(17) -0.69838(5) -0.1426(2) 0.0227(3) Uani 1 1 d . . . . .
N1 N -0.5365(2) -0.87336(6) -0.3742(3) 0.0259(4) Uani 1 1 d . . . . .
N2 N -0.3743(2) -0.77586(6) -0.4260(3) 0.0249(4) Uani 1 1 d . . . . .
C1 C -0.5555(3) -0.83507(8) -0.2245(3) 0.0241(4) Uani 1 1 d . . . . .
H1 H -0.6235 -0.8412 -0.0938 0.029 Uiso 1 1 calc R . . . .
C2 C -0.4375(3) -0.86207(8) -0.5518(3) 0.0252(4) Uani 1 1 d . . . . .
H2 H -0.4238 -0.8875 -0.6668 0.030 Uiso 1 1 calc R . . . .
C3 C -0.3536(3) -0.81442(8) -0.5742(4) 0.0260(4) Uani 1 1 d . . . . .
H3 H -0.2791 -0.8091 -0.6994 0.031 Uiso 1 1 calc R . . . .
C4 C -0.4790(2) -0.78650(8) -0.2533(3) 0.0202(4) Uani 1 1 d . . . . .
C5 C -0.5206(2) -0.74483(7) -0.0861(3) 0.0214(4) Uani 1 1 d . . . . .
C6 C -0.4936(3) -0.65665(8) 0.0028(3) 0.0208(4) Uani 1 1 d . . . . .
C7 C -0.4076(3) -0.65218(8) 0.2111(3) 0.0228(4) Uani 1 1 d . . . . .
H7 H -0.3260 -0.6777 0.2574 0.027 Uiso 1 1 calc R . . . .
C8 C -0.4442(2) -0.61023(8) 0.3454(3) 0.0225(4) Uani 1 1 d . . . . .
H8 H -0.3852 -0.6063 0.4849 0.027 Uiso 1 1 calc R . . . .
C9 C -0.5688(2) -0.57248(8) 0.2801(3) 0.0199(4) Uani 1 1 d . . . . .
C10 C -0.6142(2) -0.52983(8) 0.4204(4) 0.0227(4) Uani 1 1 d . . . . .
H10 H -0.5588 -0.5257 0.5622 0.027 Uiso 1 1 calc R . . . .
C11 C -0.7371(3) -0.49451(8) 0.3540(4) 0.0258(4) Uani 1 1 d . . . . .
H11 H -0.7657 -0.4661 0.4498 0.031 Uiso 1 1 calc R . . . .
C12 C -0.8213(3) -0.50000(8) 0.1448(4) 0.0250(4) Uani 1 1 d . . . . .
H12 H -0.9068 -0.4754 0.1006 0.030 Uiso 1 1 calc R . . . .
C13 C -0.7803(3) -0.54080(8) 0.0045(3) 0.0225(4) Uani 1 1 d . . . . .
H13 H -0.8372 -0.5441 -0.1366 0.027 Uiso 1 1 calc R . . . .
C14 C -0.6538(2) -0.57796(7) 0.0688(3) 0.0191(4) Uani 1 1 d . . . . .
C15 C -0.6115(2) -0.62114(7) -0.0701(3) 0.0204(4) Uani 1 1 d . . . . .
H15 H -0.6652 -0.6252 -0.2130 0.024 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.201(2) . ?
O2 C5 1.345(2) . ?
O2 C6 1.411(2) . ?
N1 C1 1.332(3) . ?
N1 C2 1.334(3) . ?
N2 C3 1.333(3) . ?
N2 C4 1.334(3) . ?
C1 H1 0.9500 . ?
C1 C4 1.389(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.493(2) . ?
C6 C7 1.408(3) . ?
C6 C15 1.359(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.368(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.419(3) . ?
C9 C10 1.419(3) . ?
C9 C14 1.423(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.370(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.408(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.374(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.417(3) . ?
C14 C15 1.418(2) . ?
C15 H15 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O2 C6 115.43(15) . . ?
C1 N1 C2 115.47(17) . . ?
C3 N2 C4 115.35(17) . . ?
N1 C1 H1 118.9 . . ?
N1 C1 C4 122.11(18) . . ?
C4 C1 H1 118.9 . . ?
N1 C2 H2 118.9 . . ?
N1 C2 C3 122.29(18) . . ?
C3 C2 H2 118.9 . . ?
N2 C3 C2 122.19(19) . . ?
N2 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
N2 C4 C1 122.43(17) . . ?
N2 C4 C5 119.64(17) . . ?
C1 C4 C5 117.91(17) . . ?
O1 C5 O2 124.21(17) . . ?
O1 C5 C4 123.23(17) . . ?
O2 C5 C4 112.53(16) . . ?
C7 C6 O2 119.42(17) . . ?
C15 C6 O2 117.74(17) . . ?
C15 C6 C7 122.79(18) . . ?
C6 C7 H7 120.7 . . ?
C8 C7 C6 118.53(18) . . ?
C8 C7 H7 120.7 . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.15(18) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C14 119.14(17) . . ?
C10 C9 C8 122.24(17) . . ?
C10 C9 C14 118.61(17) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.81(19) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.53(18) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.21(18) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.53(18) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C9 119.30(17) . . ?
C13 C14 C15 121.84(17) . . ?
C15 C14 C9 118.85(17) . . ?
C6 C15 C14 119.51(17) . . ?
C6 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C6 C7 C8 177.23(17) . . . . ?
O2 C6 C15 C14 -178.57(16) . . . . ?
N1 C1 C4 N2 -3.7(3) . . . . ?
N1 C1 C4 C5 174.83(18) . . . . ?
N1 C2 C3 N2 -3.7(3) . . . . ?
N2 C4 C5 O1 -177.6(2) . . . . ?
N2 C4 C5 O2 4.3(2) . . . . ?
C1 N1 C2 C3 2.7(3) . . . . ?
C1 C4 C5 O1 3.9(3) . . . . ?
C1 C4 C5 O2 -174.23(17) . . . . ?
C2 N1 C1 C4 0.8(3) . . . . ?
C3 N2 C4 C1 2.6(3) . . . . ?
C3 N2 C4 C5 -175.85(18) . . . . ?
C4 N2 C3 C2 0.9(3) . . . . ?
C5 O2 C6 C7 77.3(2) . . . . ?
C5 O2 C6 C15 -105.1(2) . . . . ?
C6 O2 C5 O1 -1.0(3) . . . . ?
C6 O2 C5 C4 177.04(15) . . . . ?
C6 C7 C8 C9 1.5(3) . . . . ?
C7 C6 C15 C14 -1.1(3) . . . . ?
C7 C8 C9 C10 177.33(18) . . . . ?
C7 C8 C9 C14 -1.4(3) . . . . ?
C8 C9 C10 C11 -178.92(18) . . . . ?
C8 C9 C14 C13 178.98(17) . . . . ?
C8 C9 C14 C15 0.1(2) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C9 C14 C15 C6 1.1(3) . . . . ?
C10 C9 C14 C13 0.2(3) . . . . ?
C10 C9 C14 C15 -178.69(17) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C12 C13 C14 C9 -0.3(3) . . . . ?
C12 C13 C14 C15 178.55(18) . . . . ?
C13 C14 C15 C6 -177.72(17) . . . . ?
C14 C9 C10 C11 -0.2(3) . . . . ?
C15 C6 C7 C8 -0.2(3) . . . . ?

_olex2_date_sample_data_collection 2015-03-25
_olex2_exptl_crystal_mounting_method 'Paratone on Cryoloop'
_olex2_submission_special_instructions 'No special instructions were received'


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1878042'
loop_
_audit_author_name
_audit_author_address
'Alireza Salimi'
;Ferdowsi University of Mashhad
Iran
;
_audit_update_record             
;
2018-11-09 deposited with the CCDC.	2019-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H6.67 N1.33 O1.33'
_chemical_formula_weight         166.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.73650(10)
_cell_length_b                   20.9912(5)
_cell_length_c                   8.5808(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.757(2)
_cell_angle_gamma                90
_cell_volume                     1209.21(4)
_cell_formula_units_Z            6
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14404
_cell_measurement_theta_min      4.1640
_cell_measurement_theta_max      75.7110

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5000
_exptl_crystal_size_mid          0.4000
_exptl_crystal_size_min          0.2500
_exptl_absorpt_coefficient_mu    0.764
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.89590
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      100(2)
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Onyx
_diffrn_detector_area_resol_mean 8.2603
_diffrn_reflns_number            33620
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.212
_diffrn_reflns_theta_max         76.222
_diffrn_reflns_theta_full        67.684
_diffrn_orient_matrix_UB_11      -0.2236160000
_diffrn_orient_matrix_UB_12      0.0039467000
_diffrn_orient_matrix_UB_13      0.0246286000
_diffrn_orient_matrix_UB_21      -0.0446172000
_diffrn_orient_matrix_UB_22      0.0204618000
_diffrn_orient_matrix_UB_23      -0.1717982000
_diffrn_orient_matrix_UB_31      -0.0258253000
_diffrn_orient_matrix_UB_32      -0.0703311000
_diffrn_orient_matrix_UB_33      -0.0486372000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2521
_reflns_number_gt                2332
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0902P)²+0.5555P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2521
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1631
_refine_ls_wR_factor_gt          0.1601
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2A O 0.16503(17) 0.31487(6) 0.01246(15) 0.0375(3) Uani 1 1 d . . . . .
C5 C -0.1407(3) 0.45102(8) -0.13911(19) 0.0343(4) Uani 1 1 d . . . . .
N2 N 0.4529(2) 0.23156(7) 0.10881(18) 0.0397(4) Uani 1 1 d . . . . .
C10 C 0.0206(2) 0.40717(8) -0.11969(19) 0.0320(4) Uani 1 1 d . . . . .
C12 C 0.3286(2) 0.21626(8) -0.0141(2) 0.0359(4) Uani 1 1 d . . . . .
C11 C 0.1517(3) 0.25792(9) -0.0568(2) 0.0418(4) Uani 1 1 d . . . . .
N1 N 0.5055(3) 0.12263(9) -0.0731(2) 0.0532(5) Uani 1 1 d . . . . .
C4 C -0.3138(3) 0.43996(9) -0.0604(2) 0.0409(4) Uani 1 1 d . . . . .
H4 H -0.4231 0.4685 -0.0757 0.049 Uiso 1 1 calc R U . . .
C1 C 0.0001(2) 0.35598(8) -0.0167(2) 0.0335(4) Uani 1 1 d . . . . .
O1 O 0.0143(3) 0.24186(9) -0.1441(3) 0.0846(7) Uani 1 1 d . . . . .
C2 C -0.1654(3) 0.34662(9) 0.0623(2) 0.0399(4) Uani 1 1 d . . . . .
H2 H -0.1716 0.3120 0.1332 0.048 Uiso 1 1 calc R U . . .
C9 C 0.1906(3) 0.41751(9) -0.2036(2) 0.0387(4) Uani 1 1 d . . . . .
H9 H 0.2971 0.3877 -0.1950 0.046 Uiso 1 1 calc R U . . .
C6 C -0.1229(3) 0.50463(9) -0.2368(2) 0.0420(4) Uani 1 1 d . . . . .
H6 H -0.2293 0.5344 -0.2500 0.050 Uiso 1 1 calc R U . . .
C8 C 0.2024(3) 0.46983(10) -0.2964(2) 0.0473(5) Uani 1 1 d . . . . .
H8 H 0.3177 0.4765 -0.3511 0.057 Uiso 1 1 calc R U . . .
C15 C 0.6058(3) 0.19151(9) 0.1391(2) 0.0422(4) Uani 1 1 d . . . . .
H15 H 0.6995 0.2000 0.2255 0.051 Uiso 1 1 calc R U . . .
C7 C 0.0444(3) 0.51423(10) -0.3120(2) 0.0487(5) Uani 1 1 d . . . . .
H7 H 0.0551 0.5510 -0.3753 0.058 Uiso 1 1 calc R U . . .
C14 C 0.6315(3) 0.13821(9) 0.0484(2) 0.0433(4) Uani 1 1 d . . . . .
H14 H 0.7437 0.1116 0.0738 0.052 Uiso 1 1 calc R U . . .
C3 C -0.3268(3) 0.38921(10) 0.0368(2) 0.0453(5) Uani 1 1 d . . . . .
H3 H -0.4451 0.3824 0.0876 0.054 Uiso 1 1 calc R U . . .
C13 C 0.3530(3) 0.16251(10) -0.1027(2) 0.0503(5) Uani 1 1 d . . . . .
H13 H 0.2578 0.1535 -0.1878 0.060 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2A C11 1.335(2) . ?
O2A C1 1.4127(19) . ?
C5 C6 1.414(3) . ?
C5 C4 1.415(3) . ?
C5 C10 1.423(2) . ?
N2 C12 1.331(2) . ?
N2 C15 1.338(2) . ?
C10 C1 1.405(2) . ?
C10 C9 1.419(2) . ?
C12 C13 1.378(3) . ?
C12 C11 1.499(2) . ?
C11 O1 1.191(2) . ?
N1 C14 1.329(3) . ?
N1 C13 1.333(3) . ?
C4 C3 1.360(3) . ?
C4 H4 0.9500 . ?
C1 C2 1.366(3) . ?
C2 C3 1.411(3) . ?
C2 H2 0.9500 . ?
C9 C8 1.363(3) . ?
C9 H9 0.9500 . ?
C6 C7 1.359(3) . ?
C6 H6 0.9500 . ?
C8 C7 1.413(3) . ?
C8 H8 0.9500 . ?
C15 C14 1.382(3) . ?
C15 H15 0.9500 . ?
C7 H7 0.9500 . ?
C14 H14 0.9500 . ?
C3 H3 0.9500 . ?
C13 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O2A C1 116.44(13) . . ?
C6 C5 C4 121.82(16) . . ?
C6 C5 C10 118.87(16) . . ?
C4 C5 C10 119.31(16) . . ?
C12 N2 C15 115.19(16) . . ?
C1 C10 C9 124.15(15) . . ?
C1 C10 C5 117.03(15) . . ?
C9 C10 C5 118.82(16) . . ?
N2 C12 C13 122.63(16) . . ?
N2 C12 C11 119.22(16) . . ?
C13 C12 C11 118.14(16) . . ?
O1 C11 O2A 123.64(17) . . ?
O1 C11 C12 123.34(17) . . ?
O2A C11 C12 113.01(14) . . ?
C14 N1 C13 115.26(17) . . ?
C3 C4 C5 121.26(16) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C2 C1 C10 123.28(16) . . ?
C2 C1 O2A 119.11(16) . . ?
C10 C1 O2A 117.49(15) . . ?
C1 C2 C3 118.83(17) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C8 C9 C10 120.55(17) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C7 C6 C5 120.89(17) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C9 C8 C7 120.44(18) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
N2 C15 C14 122.00(17) . . ?
N2 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C6 C7 C8 120.36(18) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
N1 C14 C15 122.62(17) . . ?
N1 C14 H14 118.7 . . ?
C15 C14 H14 118.7 . . ?
C4 C3 C2 120.22(17) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
N1 C13 C12 122.28(18) . . ?
N1 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C5 C10 C1 177.48(14) . . . . ?
C4 C5 C10 C1 -2.4(2) . . . . ?
C6 C5 C10 C9 -2.3(2) . . . . ?
C4 C5 C10 C9 177.77(15) . . . . ?
C15 N2 C12 C13 1.1(3) . . . . ?
C15 N2 C12 C11 179.52(17) . . . . ?
C1 O2A C11 O1 3.0(3) . . . . ?
C1 O2A C11 C12 -177.43(15) . . . . ?
N2 C12 C11 O1 -165.1(2) . . . . ?
C13 C12 C11 O1 13.5(3) . . . . ?
N2 C12 C11 O2A 15.3(3) . . . . ?
C13 C12 C11 O2A -166.15(18) . . . . ?
C6 C5 C4 C3 -178.09(17) . . . . ?
C10 C5 C4 C3 1.8(3) . . . . ?
C9 C10 C1 C2 -179.57(16) . . . . ?
C5 C10 C1 C2 0.6(2) . . . . ?
C9 C10 C1 O2A 4.4(2) . . . . ?
C5 C10 C1 O2A -175.37(13) . . . . ?
C11 O2A C1 C2 78.8(2) . . . . ?
C11 O2A C1 C10 -105.02(18) . . . . ?
C10 C1 C2 C3 1.8(3) . . . . ?
O2A C1 C2 C3 177.77(15) . . . . ?
C1 C10 C9 C8 -177.28(16) . . . . ?
C5 C10 C9 C8 2.5(2) . . . . ?
C4 C5 C6 C7 -179.68(17) . . . . ?
C10 C5 C6 C7 0.4(3) . . . . ?
C10 C9 C8 C7 -0.7(3) . . . . ?
C12 N2 C15 C14 0.0(3) . . . . ?
C5 C6 C7 C8 1.4(3) . . . . ?
C9 C8 C7 C6 -1.2(3) . . . . ?
C13 N1 C14 C15 0.7(3) . . . . ?
N2 C15 C14 N1 -1.0(3) . . . . ?
C5 C4 C3 C2 0.7(3) . . . . ?
C1 C2 C3 C4 -2.5(3) . . . . ?
C14 N1 C13 C12 0.4(3) . . . . ?
N2 C12 C13 N1 -1.4(3) . . . . ?
C11 C12 C13 N1 -179.8(2) . . . . ?

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.077

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1878043'
loop_
_audit_author_name
_audit_author_address
'Alireza Salimi'
;Ferdowsi University of Mashhad
Iran
;
_audit_update_record             
;
2018-11-09 deposited with the CCDC.	2019-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H11 N O2'
_chemical_formula_weight         249.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   7.76480(10)
_cell_length_b                   25.7822(2)
_cell_length_c                   5.89423(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1179.99(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    25524
_cell_measurement_theta_min      5.1090
_cell_measurement_theta_max      76.0070

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5000
_exptl_crystal_size_mid          0.2500
_exptl_crystal_size_min          0.2500
_shelx_estimated_absorpt_T_min   0.928
_shelx_estimated_absorpt_T_max   0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72591
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Onyx
_diffrn_detector_area_resol_mean 8.2603
_diffrn_reflns_number            31439
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.428
_diffrn_reflns_theta_max         76.190
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_orient_matrix_UB_11      -0.0355622000
_diffrn_orient_matrix_UB_12      0.1152998000
_diffrn_orient_matrix_UB_13      -0.0525495000
_diffrn_orient_matrix_UB_21      -0.0341462000
_diffrn_orient_matrix_UB_22      0.2263120000
_diffrn_orient_matrix_UB_23      0.0280315000
_diffrn_orient_matrix_UB_31      0.1922033000
_diffrn_orient_matrix_UB_32      0.0616334000
_diffrn_orient_matrix_UB_33      -0.0047529000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2459
_reflns_number_gt                2430
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.813
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0497P)²+0.2586P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1087 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.05(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2459
_refine_ls_number_parameters     172
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0811
_refine_ls_wR_factor_gt          0.0798
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2B O 0.45428(16) 0.30117(5) 0.2844(2) 0.0195(3) Uani 1 1 d . . . . .
O1 O 0.61321(18) 0.24971(5) 0.5121(2) 0.0242(3) Uani 1 1 d . . . . .
N1 N 0.5381(2) 0.12429(6) 0.0799(3) 0.0219(4) Uani 1 1 d . . . . .
C16 C 0.3878(2) 0.22061(7) -0.0144(3) 0.0203(4) Uani 1 1 d . . . . .
H16 H 0.3367 0.2533 -0.0463 0.024 Uiso 1 1 calc R U . . .
C6 C 0.6122(2) 0.47047(7) 0.8450(3) 0.0206(4) Uani 1 1 d . . . . .
H6 H 0.5550 0.4751 0.9860 0.025 Uiso 1 1 calc R U . . .
C2 C 0.4938(2) 0.34368(7) 0.4269(3) 0.0178(4) Uani 1 1 d . . . . .
C3 C 0.4028(2) 0.34959(7) 0.6319(3) 0.0193(4) Uani 1 1 d . . . . .
H3 H 0.3175 0.3251 0.6753 0.023 Uiso 1 1 calc R U . . .
C11 C 0.5249(2) 0.25510(7) 0.3462(3) 0.0178(3) Uani 1 1 d . . . . .
C15 C 0.3669(2) 0.17932(7) -0.1616(3) 0.0223(4) Uani 1 1 d . . . . .
H15 H 0.2997 0.1829 -0.2954 0.027 Uiso 1 1 calc R U . . .
C13 C 0.5544(2) 0.16420(7) 0.2215(3) 0.0202(4) Uani 1 1 d . . . . .
H13 H 0.6169 0.1590 0.3581 0.024 Uiso 1 1 calc R U . . .
C8 C 0.8223(3) 0.49892(7) 0.5705(3) 0.0219(4) Uani 1 1 d . . . . .
H8 H 0.9076 0.5233 0.5261 0.026 Uiso 1 1 calc R U . . .
C1 C 0.6144(2) 0.37817(7) 0.3550(3) 0.0181(4) Uani 1 1 d . . . . .
H1 H 0.6709 0.3734 0.2136 0.022 Uiso 1 1 calc R U . . .
C10 C 0.6549(2) 0.42148(6) 0.4941(3) 0.0172(4) Uani 1 1 d . . . . .
C5 C 0.5679(2) 0.42774(7) 0.7045(3) 0.0170(4) Uani 1 1 d . . . . .
C4 C 0.4395(2) 0.39126(7) 0.7674(3) 0.0193(4) Uani 1 1 d . . . . .
H4 H 0.3782 0.3958 0.9055 0.023 Uiso 1 1 calc R U . . .
C9 C 0.7834(2) 0.45798(7) 0.4306(3) 0.0196(4) Uani 1 1 d . . . . .
H9 H 0.8426 0.4540 0.2907 0.024 Uiso 1 1 calc R U . . .
C12 C 0.4848(2) 0.21335(7) 0.1810(3) 0.0176(4) Uani 1 1 d . . . . .
C7 C 0.7366(2) 0.50507(7) 0.7795(4) 0.0223(4) Uani 1 1 d . . . . .
H7 H 0.7652 0.5334 0.8755 0.027 Uiso 1 1 calc R U . . .
C14 C 0.4465(2) 0.13251(7) -0.1094(3) 0.0214(4) Uani 1 1 d . . . . .
H14 H 0.4352 0.1047 -0.2142 0.026 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2B C11 1.358(2) . ?
O2B C2 1.414(2) . ?
O1 C11 1.202(2) . ?
N1 C13 1.331(2) . ?
N1 C14 1.341(3) . ?
C16 C15 1.383(3) . ?
C16 C12 1.389(3) . ?
C16 H16 0.9500 . ?
C6 C7 1.370(3) . ?
C6 C5 1.420(2) . ?
C6 H6 0.9500 . ?
C2 C1 1.359(3) . ?
C2 C3 1.408(3) . ?
C3 C4 1.369(3) . ?
C3 H3 0.9500 . ?
C11 C12 1.484(2) . ?
C15 C14 1.390(3) . ?
C15 H15 0.9500 . ?
C13 C12 1.398(2) . ?
C13 H13 0.9500 . ?
C8 C9 1.373(3) . ?
C8 C7 1.409(3) . ?
C8 H8 0.9500 . ?
C1 C10 1.421(2) . ?
C1 H1 0.9500 . ?
C10 C9 1.421(2) . ?
C10 C5 1.421(2) . ?
C5 C4 1.420(2) . ?
C4 H4 0.9500 . ?
C9 H9 0.9500 . ?
C7 H7 0.9500 . ?
C14 H14 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O2B C2 115.53(14) . . ?
C13 N1 C14 116.75(16) . . ?
C15 C16 C12 118.68(16) . . ?
C15 C16 H16 120.7 . . ?
C12 C16 H16 120.7 . . ?
C7 C6 C5 120.74(18) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C1 C2 C3 122.85(16) . . ?
C1 C2 O2B 118.13(17) . . ?
C3 C2 O2B 118.98(16) . . ?
C4 C3 C2 118.77(17) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
O1 C11 O2B 123.33(16) . . ?
O1 C11 C12 124.69(16) . . ?
O2B C11 C12 111.95(15) . . ?
C16 C15 C14 118.52(17) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
N1 C13 C12 123.87(17) . . ?
N1 C13 H13 118.1 . . ?
C12 C13 H13 118.1 . . ?
C9 C8 C7 120.51(17) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C2 C1 C10 119.16(17) . . ?
C2 C1 H1 120.4 . . ?
C10 C1 H1 120.4 . . ?
C1 C10 C9 121.60(17) . . ?
C1 C10 C5 119.17(16) . . ?
C9 C10 C5 119.22(16) . . ?
C4 C5 C6 122.11(17) . . ?
C4 C5 C10 119.10(16) . . ?
C6 C5 C10 118.79(16) . . ?
C3 C4 C5 120.91(17) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C8 C9 C10 120.34(17) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C16 C12 C13 118.26(16) . . ?
C16 C12 C11 124.03(15) . . ?
C13 C12 C11 117.68(16) . . ?
C6 C7 C8 120.40(17) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
N1 C14 C15 123.87(17) . . ?
N1 C14 H14 118.1 . . ?
C15 C14 H14 118.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 O2B C2 C1 102.67(19) . . . . ?
C11 O2B C2 C3 -79.6(2) . . . . ?
C1 C2 C3 C4 -1.4(3) . . . . ?
O2B C2 C3 C4 -178.95(16) . . . . ?
C2 O2B C11 O1 1.1(3) . . . . ?
C2 O2B C11 C12 -176.86(14) . . . . ?
C12 C16 C15 C14 -1.1(3) . . . . ?
C14 N1 C13 C12 -1.2(3) . . . . ?
C3 C2 C1 C10 1.7(3) . . . . ?
O2B C2 C1 C10 179.34(15) . . . . ?
C2 C1 C10 C9 178.20(17) . . . . ?
C2 C1 C10 C5 -0.2(2) . . . . ?
C7 C6 C5 C4 -179.90(17) . . . . ?
C7 C6 C5 C10 -0.1(3) . . . . ?
C1 C10 C5 C4 -1.7(2) . . . . ?
C9 C10 C5 C4 179.91(16) . . . . ?
C1 C10 C5 C6 178.50(16) . . . . ?
C9 C10 C5 C6 0.1(2) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C6 C5 C4 C3 -178.10(17) . . . . ?
C10 C5 C4 C3 2.1(3) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
C1 C10 C9 C8 -178.70(17) . . . . ?
C5 C10 C9 C8 -0.3(3) . . . . ?
C15 C16 C12 C13 -1.1(3) . . . . ?
C15 C16 C12 C11 176.59(18) . . . . ?
N1 C13 C12 C16 2.4(3) . . . . ?
N1 C13 C12 C11 -175.48(17) . . . . ?
O1 C11 C12 C16 -177.51(19) . . . . ?
O2B C11 C12 C16 0.4(2) . . . . ?
O1 C11 C12 C13 0.2(3) . . . . ?
O2B C11 C12 C13 178.15(16) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C9 C8 C7 C6 -0.5(3) . . . . ?
C13 N1 C14 C15 -1.2(3) . . . . ?
C16 C15 C14 N1 2.4(3) . . . . ?

_refine_diff_density_max         0.140
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.042

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_III
_database_code_depnum_ccdc_archive 'CCDC 1879690'
loop_
_audit_author_name
_audit_author_address
'Ali Samie'
;Ferdowsi University of Mashhad
Iran
;
_audit_update_record             
;
2018-11-18 deposited with the CCDC.	2019-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        '1-naphtyl pyridine-2-carboxylate'
_chemical_name_common            III
_chemical_melting_point          344.4
_chemical_formula_moiety         'C16 H11 N O2'
_chemical_formula_sum            'C16 H11 N O2'
_chemical_formula_weight         249.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.21(4)
_cell_length_b                   8.42(2)
_cell_length_c                   20.22(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2590(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4498
_cell_measurement_theta_min      1.7
_cell_measurement_theta_max      33.6

_exptl_crystal_description       Cuboid
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.637
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  Molybdenum
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 13.6612
_diffrn_reflns_number            21840
_diffrn_reflns_av_unetI/netI     0.1084
_diffrn_reflns_av_R_equivalents  0.1686
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.014
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2545
_reflns_number_gt                2232
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)'
_computing_cell_refinement       
'CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)'
_computing_data_reduction        
'CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1655P)²+0.8503P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2545
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0991
_refine_ls_wR_factor_ref         0.3057
_refine_ls_wR_factor_gt          0.2867
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_restrained_S_all      1.168
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.82289(15) 0.9409(4) 0.82462(12) 0.0997(11) Uani 1 1 d . . . . .
O2A O 0.90952(13) 0.8433(3) 0.90526(10) 0.0660(7) Uani 1 1 d . . . . .
N1 N 0.60824(17) 0.9457(4) 0.95157(15) 0.0798(9) Uani 1 1 d . . . . .
C1 C 0.98114(18) 0.8360(4) 0.86040(14) 0.0584(7) Uani 1 1 d . . . . .
C2 C 1.0000(2) 0.6978(4) 0.82944(16) 0.0652(8) Uani 1 1 d . . . . .
H2 H 0.964858 0.609129 0.836715 0.078 Uiso 1 1 calc R U . . .
C3 C 1.0728(2) 0.6869(4) 0.78604(16) 0.0687(9) Uani 1 1 d . . . . .
H3 H 1.085220 0.591971 0.764430 0.082 Uiso 1 1 calc R U . . .
C4 C 1.12522(19) 0.8188(4) 0.77615(15) 0.0666(9) Uani 1 1 d . . . . .
H4 H 1.173345 0.812257 0.747911 0.080 Uiso 1 1 calc R U . . .
C5 C 1.10614(17) 0.9650(4) 0.80893(14) 0.0580(7) Uani 1 1 d . . . . .
C6 C 1.1580(2) 1.1025(5) 0.7993(2) 0.0773(10) Uani 1 1 d . . . . .
H6 H 1.207104 1.097271 0.771968 0.093 Uiso 1 1 calc R U . . .
C7 C 1.1378(3) 1.2407(5) 0.8290(3) 0.0934(13) Uani 1 1 d . . . . .
H7 H 1.172286 1.329834 0.820878 0.112 Uiso 1 1 calc R U . . .
C8 C 1.0671(3) 1.2528(5) 0.8712(2) 0.0920(13) Uani 1 1 d . . . . .
H8 H 1.054576 1.350025 0.890951 0.110 Uiso 1 1 calc R U . . .
C9 C 1.0142(2) 1.1232(5) 0.88488(19) 0.0766(10) Uani 1 1 d . . . . .
H9 H 0.967548 1.132200 0.914387 0.092 Uiso 1 1 calc R U . . .
C10 C 1.03261(17) 0.9729(4) 0.85244(14) 0.0582(8) Uani 1 1 d . . . . .
C11 C 0.83197(18) 0.8939(4) 0.88068(15) 0.0620(8) Uani 1 1 d . . . . .
C12 C 0.76059(19) 0.8931(4) 0.93133(14) 0.0622(8) Uani 1 1 d . . . . .
C16 C 0.7707(3) 0.8388(6) 0.99549(17) 0.0941(14) Uani 1 1 d . . . . .
H16 H 0.825208 0.804750 1.010811 0.113 Uiso 1 1 calc R U . . .
C15 C 0.6978(3) 0.8367(7) 1.0361(2) 0.1079(15) Uani 1 1 d . . . . .
H15 H 0.702225 0.799361 1.079310 0.129 Uiso 1 1 calc R U . . .
C14 C 0.6192(2) 0.8896(5) 1.01246(19) 0.0805(10) Uani 1 1 d . . . . .
H14 H 0.570676 0.886388 1.040387 0.097 Uiso 1 1 calc R U . . .
C13 C 0.67894(19) 0.9474(5) 0.91282(16) 0.0718(9) Uani 1 1 d . . . . .
H13 H 0.672707 0.988007 0.870313 0.086 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.209(5) . ?
O2A C11 1.349(4) . ?
O2A C1 1.419(4) . ?
N1 C13 1.331(5) . ?
N1 C14 1.329(6) . ?
C1 C2 1.352(5) . ?
C1 C10 1.403(5) . ?
C2 C3 1.416(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.428(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.415(5) . ?
C5 C10 1.425(5) . ?
C6 C7 1.345(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.378(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.383(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.453(6) . ?
C9 H9 0.9300 . ?
C11 C12 1.492(5) . ?
C12 C13 1.375(5) . ?
C12 C16 1.384(5) . ?
C16 C15 1.381(6) . ?
C16 H16 0.9300 . ?
C15 C14 1.362(7) . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O2A C1 116.7(3) . . ?
C13 N1 C14 116.6(3) . . ?
C2 C1 C10 122.4(3) . . ?
C2 C1 O2A 119.8(3) . . ?
C10 C1 O2A 117.8(3) . . ?
C1 C2 C3 120.6(3) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 119.3(3) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C10 119.0(3) . . ?
C6 C5 C4 121.9(3) . . ?
C10 C5 C4 119.1(3) . . ?
C7 C6 C5 121.3(4) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 121.3(4) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C9 C8 C7 121.3(4) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 119.0(4) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C1 C10 C5 118.1(3) . . ?
C1 C10 C9 123.8(3) . . ?
C5 C10 C9 118.1(3) . . ?
O1 C11 O2A 123.3(3) . . ?
O1 C11 C12 124.2(3) . . ?
O2A C11 C12 112.5(3) . . ?
C13 C12 C16 117.7(3) . . ?
C13 C12 C11 118.0(3) . . ?
C16 C12 C11 124.3(3) . . ?
C12 C16 C15 118.2(4) . . ?
C12 C16 H16 120.9 . . ?
C15 C16 H16 120.9 . . ?
C14 C15 C16 119.4(4) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
N1 C14 C15 123.5(3) . . ?
N1 C14 H14 118.2 . . ?
C15 C14 H14 118.2 . . ?
N1 C13 C12 124.5(3) . . ?
N1 C13 H13 117.8 . . ?
C12 C13 H13 117.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 O2A C1 C2 -94.7(4) . . . . ?
C11 O2A C1 C10 88.3(3) . . . . ?
C10 C1 C2 C3 -1.2(5) . . . . ?
O2A C1 C2 C3 -178.1(3) . . . . ?
C1 C2 C3 C4 0.7(5) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C3 C4 C5 C6 -179.4(3) . . . . ?
C3 C4 C5 C10 0.5(4) . . . . ?
C10 C5 C6 C7 -1.8(5) . . . . ?
C4 C5 C6 C7 178.0(3) . . . . ?
C5 C6 C7 C8 1.6(6) . . . . ?
C6 C7 C8 C9 0.2(7) . . . . ?
C7 C8 C9 C10 -1.7(6) . . . . ?
C2 C1 C10 C5 1.3(4) . . . . ?
O2A C1 C10 C5 178.2(2) . . . . ?
C2 C1 C10 C9 179.9(3) . . . . ?
O2A C1 C10 C9 -3.1(4) . . . . ?
C6 C5 C10 C1 179.0(3) . . . . ?
C4 C5 C10 C1 -0.9(4) . . . . ?
C6 C5 C10 C9 0.2(4) . . . . ?
C4 C5 C10 C9 -179.6(3) . . . . ?
C8 C9 C10 C1 -177.2(3) . . . . ?
C8 C9 C10 C5 1.5(5) . . . . ?
C1 O2A C11 O1 -4.6(5) . . . . ?
C1 O2A C11 C12 178.5(3) . . . . ?
O1 C11 C12 C13 0.9(5) . . . . ?
O2A C11 C12 C13 177.8(3) . . . . ?
O1 C11 C12 C16 179.8(4) . . . . ?
O2A C11 C12 C16 -3.3(5) . . . . ?
C13 C12 C16 C15 2.4(7) . . . . ?
C11 C12 C16 C15 -176.4(4) . . . . ?
C12 C16 C15 C14 -1.0(8) . . . . ?
C13 N1 C14 C15 0.5(7) . . . . ?
C16 C15 C14 N1 -0.6(8) . . . . ?
C14 N1 C13 C12 1.2(6) . . . . ?
C16 C12 C13 N1 -2.7(6) . . . . ?
C11 C12 C13 N1 176.3(3) . . . . ?

_refine_diff_density_max         0.775
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.080


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane and Ethyl Acetate'
